Potassium Carbonate → 8-(cyclopentyloxy)-3-methyl-7-((4-methylthiazol-2-yl)methyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200680Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200680
[CH:1]1([O:6][C:7]2[NH:15][C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[CH2:30][C:31]1[S:32][CH:33]=[C:34]([CH3:36])[N:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH:1]1([O:6][C:7]2[N:15]([CH2:30][C:31]3[S:32][CH:33]=[C:34]([CH3:36])[N:35]=3)[C:14]3[C:13](=[O:16])[N:12]([CH2:17][CH2:18][CH2:19][O:20][CH:21]4[CH2:26][CH2:25][CH2:24][CH2:23][O:22]4)[C:11](=[O:27])[N:10]([CH3:28])[C:9]=3[N:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 112750912-(Chloromethyl)-4-methyl-1,3-thiazole2×HCID 904028818-(cyclopentyloxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 904029518-(cyclopentyloxy)-3-methyl-7-((4-methylthiazol-2-yl)methyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 8-(cyclopentyloxy)-3-methyl-1-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1H-purine-2,6(3H,7H)-dione (0.12 g, 0.31 mmol) in DMF (5 mL) was added 2-(chloromethyl)-4-methylthiazole (91 mg, 0.62 mmol, intermediate 54), potassium carbonate (85 mg, 0.62 mmol), and TBAI (2 mg, 0.02 mmol). The reaction was heated at 50° C. overnight. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product which was used without purification. LCMS retention time 1.704 min; LCMS MH+-THP 470.

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a119737ef4d248ff98d667da65813883
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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